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Boston, Cape Cod & The Islands - Classic Group

Tour, Escorted tour
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Boston, Cape Cod & The Islands - Classic Group
This 8-Day guided tour blends history with glamour as you travel from Massachusetts to Rhode Island. Follow the red-brick Freedom Trail in Boston to see where the U.S. took shape. On the shores of Cape Cod Bay, see Sandwich, a coastal town famous for its glassmakers; here, visit the Sandwich Glass Museum, where you can learn tricks of the trade. At Martha's Vineyard, a driver will take you past the former home of Jacqueline Kennedy Onassis and to Oak Bluffs, an idyllic town with gingerbread-like cottages. Indulge in a sea-to-table feast filled with fish caught from local fishermen, fresh produce from nearby farms and delicacies picked by foragers. In the seaside city of Newport, board an 80-foot schooner to cruise the coastline, taking in views of historical buildings and the homes of the rich and famous - and learn about the area’s past as a pirates’ haven.


Dining Summary
  • 4 Dinner with Wine (DW)
  • 7 Breakfast (B)
Choice Highlights
  • Boston: Step through the hallowed gates and enter Fenway Park. Home to the nine-time World Series winning Boston Red Sox since 1912, Fenway is the oldest baseball stadium in America. Enjoy an in depth one-hour guided tour of the legendary sports history that has taken place here, with a chance to visit the press box, view memorabilia, and sit in the fabled ‘Green Monster’ overlooking left field. You will be sure to feel the electric energy of the stadium that represents America’s favorite pastime.
  • Boston: Visit the Museum of Fine Arts, renowned for its Impressionist paintings, Asian and Egyptian collections and early American art.
Authentic Dining
  • Boston: At 18:00, join your Travel Director for a dinner with wine and an opportunity to mingle with fellow guests.
  • Martha's Vineyard: Tonight's Sea-to-Table dinner at Menemsha Room is sure to delight with the season’s freshest offerings from local farms, fishing boats, foragers and markets.
  • Newport: Meet your new friends in the evening for a seafood dinner with wine, where you can share the highlights of your trip while savoring a freshly prepared meal.
Insight Choice
  • Boston: Step through the hallowed gates and enter Fenway Park. Home to the nine-time World Series winning Boston Red Sox since 1912, Fenway is the oldest baseball stadium in America. Enjoy an in depth one-hour guided tour of the legendary sports history that has taken place here, with a chance to visit the press box, view memorabilia, and sit in the fabled ‘Green Monster’ overlooking left field. You will be sure to feel the electric energy of the stadium that represents America’s favorite pastime.
  • Boston: Visit the Museum of Fine Arts, renowned for its Impressionist paintings, Asian and Egyptian collections and early American art.
Insight Experiences
  • Newport: Jump onboard the Adirondack II, an 80-foot schooner sailing ship and cruise around the coastline. You’ll sail out and pass nearby islands, old historical buildings and homes of the rich and famous, as you learn about the region’s exciting history, including its pirate activity.
  • Newport: Enjoy a visit to one of Newport's renowned landmarks, The Vanderbilt's Breakers Mansion.
Make Travel Matter
  • Plymouth: Visit the Plimoth Patuxet (Puh – tux- it) Museum – which is really more like a living memorial dedicated to the lifestyle of the first English settlers and the Wampanoag Indigenous community. Enjoy a guided journey to the early homesite of the Wompanoag people, a living version of the early English settlement village and a full scale replica of the Mayflower 2 – the ship that made the initial voyage in 1620. By visiting, we’re helping the museum preserve the histories and stories of the early inhabitants and the revitalization of pre-industrial crafts, trades, domestic skills, horticulture, and maritime arts.Your experience advances UN Global Goals 10 & 11: Reduced Inequalities & Sustainable Cities and Communities.
Top Rated Highlights
  • Boston: Explore the great city of Boston, with your Travel Director and learn about its transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. Journeying to other historically significant sights that include the Boston Common, the Old Corner Bookstore and the Bunker Hill Monument in Charlestown. View the colorful neighborhood of Back Bay and the lively North End, otherwise known as Boston’s Little Italy.
  • Plymouth: Visit Pilgrim Hall Museum, the oldest continuously operating public museum in the country and America’s museum of Pilgrim possessions. Meet a direct descendant of the Mayflower party that landed on America's shores in 1620 and hear their family stories.
  • Sandwich: View through the lens of the skilled craftsmen at the Sandwich Glass Museum, where you will learn the techniques of the English and Irish glass-makers developed during the early 19th century.
  • Cape Cod: Experience the natural wonder and human history emphasizing the cultural themes represented on Cape Cod, including the First People--the Wampanoag; European settlement culture; fishing, life-saving, and lighthouses; communication technology of Cape Cod's National Seashore.
  • Martha's Vineyard: After disembarking from your ferry ride, visit the port neighborhood of Oak Bluffs and be transported to a different era. Known for its rainbow-colored, gingerbread-like cottages with Gothic storybook decorations, high-peaked roofs, and dainty verandas. You’ll also find the oldest operating platform carousel in America here.
  • Nantucket: Walk through historic downtown Nantucket and discover the unique history of the island. Journey through Nantucket’s past and hear about the rise and the fall of the whaling industry, the rise of tourism, and the impacts the island’s economy has had on social and racial development on Nantucket.

About Insight Vacations
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There's more to travel than simply visiting new places – join us for experiences that spark your curiosity and take you beyond traditional sightseeing. On our premium guided tours, every day is filled with fascinating facts and intriguing stories, while superior dining nourishes the body and stylish hotels rest the soul.

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Discover the superior touring experience you deserve.

Oct 11, 2024 through
Oct 18, 2024
Oct 7, 2024 7:00 PM
7 Nights from
$4,034.00 (USD)
Per Person
Please Call, Book by 2024-10-04 to receive $711.00 Last Minute Deal Discount. Airfare not included
Last Minute Deal: Must book by 2024-10-04
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Prices are per-person based on double occupancy, unless otherwise noted.